Beach house holiday rentals in Middle River

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

Peaceful Waterfront Oasis

This peaceful Chesapeake Bay retreat offers an escape from daily life, with stunning bay views providing a calming backdrop at sunrise and sunset. Relax on the deck with coffee, swim right off the dock, or unwind by the water’s edge. For adventure, take out the available kayaks or paddle board to explore the tranquil bay. Afterward, enjoy a rinse in the outdoor shower and soak in the hot tub under the stars. This serene haven blends relaxation and adventure in a beautiful, picturesque setting.

The Havre de Grace Bay House

Visit the lovely and Historic town of Havre de Grace and stay on the beautiful Chesapeake Bay! The house features four bedrooms ,a well appointed kitchen,four bathrooms, living rooms, library, basement with separate living space. The outside includes a large deck with seating areas ,gas grill, and a breathtaking view of the bay . The town offers restaurants, bars, coffee, shops, ice cream, and homemade candy. First Friday and Saturday markets with vendors throughout the spring and summer.

Waterfront 2-Acre Retreat Panoramic Views

Escape to The Cove at Heron Point, a private waterfront retreat on two peaceful acres along Maryland's Eastern Shore. Wake to breathtaking sunrises, kayak from the property, unwind in our unique greenhouse sauna (coming fall 2026!), gather around the fire pit, and create lasting memories with family and friends. Designed for relaxation, adventure, and connection, it's the perfect escape for every season in the heart of Kent Narrows, minutes to waterfront dining and Chesapeake adventures.

Sunset at Rabbit Run

Sunset at Rabbit Run is a private waterfront 2 acre property located on the Chesapeake Bay with a semi private beach area and fabulous sunsets. Located just outside of the quaint town of Rock Hall with shade trees in the summer. Fish, crab, kayak and swim in the Chesapeake Bay (weather permitting) while enjoying fabulous sunsets, read a book on the hammock or watch the boats up and down the Chesapeake as they enter Rock Hall Harbor. Your family and/or friends will never want to leave.

Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

Waterfront 5 Bedroom Near BWI/Annapolis/Baltimore

Welcome to your private waterfront escape—a 5-bedroom, 2.5-bath oasis nestled on the serene shores of Stoney Creek. Located just 20 minutes from BWI Airport, downtown Annapolis (US Naval Academy), and Baltimore, this stunning home offers the perfect blend of comfort, convenience, and coastal charm. Weather you are preparing for your wedding, planning a family getaway, a friends’ weekend, or a peaceful retreat, you’ll find the space, amenities, and setting here to make it unforgettable.

Chesapeake Bay Estate; 2 Houses, Beach&Heated Pool

House and Guest House with heated in-ground swimming pool -perfect for 2 families or extended family gatherings 15 acres of wooded grounds,350 feet of waterfront, very private Main house 3 bedrooms - 2 full baths Guest house 3 bedrooms - 2 full baths including large semi-outdoor shower Hot tub overlooking Bay Screened porch, Bay & Pondside decks Sandy Beach on Still Pond Cove and Chesapeake Bay, 150 ft. pier The pool will be closed as of mid-October and will reopen early May 2021

Waterfront Wellness - *With Pool and Hot Tub!*

Welcome To Paradise! 🌊 Private Beach | 🏊 Heated Pool | 🔥 Sauna | 💦 Hot Tub| 🌅 Sunset Views This Chesapeake Bay retreat features a private beach, heated pool, sauna, hot tub, and guest house in a peaceful waterfront neighborhood. Enjoy coffee on the deck, afternoons swimming or kayaking, and evenings watching sailboats pass as the sun sets over the bay. Just minutes from historic downtown Chestertown, shops, restaurants, and marinas for the perfect Eastern Shore getaway.

Goose Haven, new waterfront house on Fairlee Creek

Goose Haven is nestled on 2 wooded acres on freshwater, Fairlee Creek - about 1.5 hours from Baltimore, Philadelphia, and Washington D.C. It is a very secluded, brand new, 4 BR, 3 BA, waterfront house with direct water access, a dock, and plenty of room to enjoy the outdoors. There is also a public boat ramp/launch right down the road. If you don’t have a boat, don’t worry, we have a kayak & canoe for you to use. Chestertown and Rock Hall are only 20 minutes away.

Top of the Chesapeake - Private Waterfront Home

Our house is nestled between the shore of the NE River and the creek and marsh directly behind. The home is warm, unassuming and inviting; you'll feel right at home. Perfect for familes or groups, or a romantic weekend. Bird watchers will love the bald eagles, ospreys, kingfishers, mallards and cormorants, to name a few. The upstairs living room is a perfect place for the kids while the adults enjoy the lower area. You find our place warm, cozy and quiet.

Mac's Waterfront Wonder

Your family will be wowed by this NEW waterfront 5 bedroom home with a home office, TWO balconies. Indulge in birdwatching (spot a bald eagle? ), boating and jet skiing! Visit Baltimore, DC, Philly, Golf and more! This new home is ideal for large families, long-term stays, or remote work. Three Queen beds; two twins and a bunk bed (full + twin). Sofa bed/queen and air mattresses for five more guests at an additional cost.